How I Made the Switch from Traditional Employment to Freelancing and How You Can, Too

I majored in English in college. 

(Honestly, this is probably the worst decision I have ever made.  If I had to do it over again, I’d probably major in something more practical like journalism where I could still utilize my love of reading and writing.)

I went on to graduate school where I majored in English and Teaching English as a Second Language.  One year after I graduated, I snagged a job as a full-time English composition teacher at a community college outside an urban area.

In the beginning, I loved teaching even though the load was heavy.  I was expected to teach 5 classes a semester; each class had 28 students.  Each student had to write five essays during the semester.  That means I was grading 700 essays in a 16 week period.  These essays were each 3 to 4 pages long.

The load was heavy but manageable before I had children.  But when I had my son four years after I got the job, I started having difficulty balancing my work life with my home life.

By the time I had my second child four years later, I no longer enjoyed my job.

The quality of students was deteriorating.  The school hired full-time security guards to roam the halls because there had been so many problems with students threatening teachers and fighting in the classrooms.

In addition, the political environment on campus was difficult.  I was ready to quit, but because my husband was finishing his Ph.D., I was the sole breadwinner.

Seventeen months after we had our second child, we had our third.  I was granted a generous 16 month leave of absence.  My husband and I decided that we would do what we had to do to make sure I didn’t have to go back to my job.

How I made the switch to freelancing.

Finding Work as a Freelancer

Ten months into my sixteen month leave of absence, I got my first freelance writing job right here on Free From Broke.

Thanks to this job, a few other bloggers saw my work and offered me freelance writing jobs.  Over the next year the snowball effect continued until I had as many freelance writing jobs as I could handle while still caring for two very young children during the day.

There are several things that helped me grow my business:

Find Your Tribe

Find a group of people whose interests are similar to your own.  I found a blog group and became an active member.  Glen was also a member, and when I asked how to get started as a freelancer on the forum, he offered me a tentative position.

Another suggestion is to join groups where your potential clients gather [Glen: LinkedIn and Facebook can be great for this].  The trick is not to specifically ask for work but to instead answer questions and be as helpful as possible.  People will notice and remember you and eventually come to you with job recommendations.

Find Mentors To Show You The Ropes

One more way to find your tribe is to join a group of mentors.  For instance, if you’d like to be a freelance writer, join a group where freelance writers converge.  For awhile, I was part of The Writer’s Den, and online forum for writers.  I could ask questions, and more experienced writers would gladly help and guide me.

Don’t be afraid to e-mail someone in your field whose work you admire.  I’ve done this a few times, and most people are more than happy to answer your questions and provide guidance.  Now that I’ve been freelancing for three years, I sometimes have people e-mail me for advice, and I gladly give it.

Make Friends

Try not to think of others who are doing the same work as you as your competitors.  Instead, try to think of them as potential partners.  If you can befriend a few of them, you can work on projects together and grow each of your businesses.  Or, if you get offered a job you can’t accept, you can refer it to your friend, and she can do the same for you.

Just Ask

This almost sounds too easy, but it sometimes works.

Ask a company if they need someone who does what you do.  This works best if you find a company who appears to be in need of the services you offer.

For instance, if you are a freelance writer, did you come across a company blog that is updated only every four months or so?  Why not send a note of introduction and mention the services you could provide for the company.  The worst you could hear is, “No thanks.”

Juggling Time and Jobs

When you first start freelancing, you probably don’t think you’ll ever see a day where you have too much work to do.  Yet, if you do good work as a freelancer, the jobs should keep coming in.  Eventually, you’ll need to learn how to say no to some jobs.  Otherwise you’ll run the risk of falling behind on your work and disappointing the clients you already have.

When deciding which old clients to keep if I need to make way for a new client, I consider how easy the person is to work for, how much the client pays, what our relationship is like, and how much exposure I get from the position.  Clients who are difficult to work with are the easy first choice for elimination.  Luckily, I haven’t had too many of those.

Increasing Income

As a freelancer, there are two ways to increase your income.

You can take more jobs, or you can earn more from the jobs you already have.  Since you have a finite amount of time, taking more jobs can only get you so far.

However, when you do take on a new job, make sure to quote a price for the work that is higher than what you’re currently being paid.  That not only gives you room to negotiate, but it also helps you earn more as time goes on.  Every new client should theoretically pay more than the clients you currently have.

Even with this strategy, though, the time will come when you need to ask existing clients for a raise.  This makes some freelancers uncomfortable, but doing so is necessary.

If you don’t mind losing the client, you can send a polite e-mail stating that the client is currently paying you your lowest rate and that you are requesting a raise.  If the client can’t increase your pay, you understand, but you’ll need to quit the job by a certain date.  Each time I’ve used this strategy, I have gotten a raise.  Sometimes I ask for a specific raise and sometimes I leave it open ended so the client can determine how much the raise should be.

If you don’t want to lose the client, you can ask for a raise, but do so after careful consideration.  If the client says no and you stay on the job, chances are you won’t likely get a raise from this client in the future.

Taking Care of the Behind the Scenes Work

Unfortunately, freelancing is only one part of the equation.  You must also take care of the backside of the business–accounting and taxes, primarily.

Keeping Up with the Books

I do most of my bookkeeping myself with Quickbooks, but I also hire a bookkeeper to go over my books to make sure that I did everything correctly.  I also hire an accountant to do my taxes.

Paying Quarterly Taxes

One huge downside of freelancing is that you’ll need to pay quarterly taxes.  My accountant estimates how much my quarterly taxes are, and I pay them four times a year.  I put aside 1/12 of the taxes due for a year each month.  This takes discipline, but if you don’t put aside the money monthly, you’ll face a serious financial problem when you suddenly need to find the money to pay the quarterly tax bill on time.

If you’re used to getting a tax refund each year, that will likely end once you start freelancing.  If everything goes well, you should just break even at tax time.

Note: Another option is to incorporate as an S-Corp.  With this you pay yourself a fair salary and your employment taxes get paid through your paycheck.  Talk with an accountant about your business to see what business entity works best for your situation.

Final Thoughts On Becoming a Freelancer

This month marks three years since I started freelancing.

I’m glad that I was able to quit my job and that I now earn as much money working from home and caring for my kids as I would have earned had I stayed at my job and had to pay for two small children in daycare.

Being a freelancer isn’t for everyone.

You need to be self-motivated and disciplined.  You need to be able to approach people about potential jobs and raises.

However, I love the flexibility freelancing gives me, and I’d recommend a non-traditional job like this for anyone who wants to work from home and take care of their children while earning an income.

Do you freelance?  What do you like most and least about freelancing?

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Published or updated March 6, 2014.


  1. I freelance full-time now, and I would never go back. Life is so much better due to so many different reasons. I really love having a flexible schedule and being able to do something that I enjoy!

  2. I especially love the tip “Make friends”. This post is great for freelancers but also for anyone thinking of becoming self-employed or an entrepreneur. Thanks for the reminders!

    • Glen Craig says:

      Know what? Making friends and networking is great advice for anyone even you you don’t plan on freelancing or starting your own business. So many people get jobs based on their connections and network of friends.

  3. I feel you have to build up contacts so then that way you can share work amongst yourselves and if one person in your contact list discovers a new income stream they’ll more then likely share it with you.

  4. As one of the many people who pays Melissa to write for their site (100 articles and counting! ), her quality of work is consistently top notch, and she understands how to do a job and do it well. I don’t know how freelancers like yourself do it – as far as juggling all your writing jobs, and still maintaining a high quality of writing. When you have a high quality product like you do – you’ll always be in demand.

    I agree finding people who are in a similar niche and/or interests to your own is important, and engaging with folks and getting to know them a bit first. A lot of times those casual relationships can lead to jobs, and help in finding other jobs down the road.

  5. Freelancing can be a great option for the right person. Its got some challenges, but if you can keep at it long enough, and stay on top of your bookkeeping, it can be quite rewarding. I’m glad to hear its working well for you!

  6. Excellent post Melissa! My wife did something very similar a little over four years ago and left her job after having our second child and started freelance writing on the side. Over time, it has turned in to our business that we now both run. We love it as we can control, to a certain extent, what work we do and can dictate our own schedule. Dealing with demanding clients isn’t always the most fun, but is well worth the trade off.

  7. I think one of the key things for me to be successful would be to find that tribe and some mentors. Trying to figure this all out on your own can be a daunting task. I like that you have these at the top of the list.

  8. Thanks for this great article! Making the jump to freelancing can be very challenging, and it’s great to have a walkthrough guide such as this!

  9. One of the great things about us writers is generally we keep together, admire and encourage one another – so it’s true you should look to make friends and be helpful and social online with others.
    Finding a niche and people equally passionate about it is the first step on the road to success. Another way to put is; be a geek and look for other geeks to recruit you. Geeks being cool, of course.

    Great article, thanks.

  10. I started to become a freelancer four years ago, and I’m so happy about my decision. I can control my own time , I have more time with my daughter and the good thing is that I can wear my pajamas all day! My hubs told me that he wants to quit his job, he has been working as a Software Engineer in a good company for 5 years and he said that he really wants to become a freelancer too.

  11. It seems as though many bloggers want to become freelancers when they start blogging, and many of them end up quitting their day jobs to become freelancers. I would love the freedom of being able to work for myself, but at the same time, I think I would put in a lot more hours, which would be frustrating. I’ve been indecisive about whether I eventually want to venture out on my own. I am glad it worked out for you, though!

    • Glen Craig says:

      I think for many who have been able to successfully quit their ‘traditional’ jobs they started out small, working on the side. If you think it’s something that’s for you then you can use your off-hours to start building things up.

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